Potassium Carbonate → HCID 86663027, compound

Participants

Reaction Steps

A suspension of methyl 7-hydroxy-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (800 mg, 2.07 mmol), 4-nitrophenyl trifluoromethanesulfonate (842 mg, 3.11 mmol), and potassium carbonate (859 mg, 6.21 mmol) in DMF (12 ml) was stirred at RT for 3 hr. The reaction was partitioned between water and EtOAc. The organic phase was separated and washed with water (5×) and brine. It was dried with sodium sulfate and the solvent was removed. Column chromatography (step gradient elution with hexane containing 20 to 80% DCM) afforded methyl 2-(3-(trifluoromethyl)phenyl)-7-(trifluoromethylsulfonyloxy)-5H-pyrido[3,2-b]indole-4-carboxylate (548 mg, 1.06 mmol, 51% yield) as a light yellow solid. MS (ESI) m/z 587.09 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.76 (1H, s), 8.51 (1H, d, J=8.55 Hz), 8.44 (1H, s), 8.31-8.38 (2H, m), 7.60-7.72 (2H, m), 7.51 (1H, d, J=2.14 Hz), 7.29 (1H, dd, J=8.55, 2.14 Hz), 4.13 (3H, s).

Provenance & Evidence